CN106753156A - A kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof - Google Patents

A kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof Download PDF

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Publication number
CN106753156A
CN106753156A CN201611240127.6A CN201611240127A CN106753156A CN 106753156 A CN106753156 A CN 106753156A CN 201611240127 A CN201611240127 A CN 201611240127A CN 106753156 A CN106753156 A CN 106753156A
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Prior art keywords
sulfonic acid
acid type
chain extender
preparation
environment protection
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Chinese (zh)
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羊梦诗
廖平永
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Jiaxing Deyang Biotechnology Co Ltd
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Jiaxing Deyang Biotechnology Co Ltd
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Priority to CN201611240127.6A priority Critical patent/CN106753156A/en
Publication of CN106753156A publication Critical patent/CN106753156A/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44Polycarbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633Compounds of group C08G18/42
    • C08G18/6637Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633Compounds of group C08G18/42
    • C08G18/6637Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6648Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6651Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The present invention discloses a kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof, is prepared by each component of following weight portion:100 parts of polycarbonate polyol, 50 ~ 70 parts of diisocyanate, 0.5 ~ 1.5 part of small molecule chain extender, 0.02 ~ 0.1 part of dibutyl tin laurate, 10 ~ 25 parts of organic solvent, 1 ~ 10 part of sulfonic acid type hydrophilic chain extender, 150 ~ 250 parts of deionized water;Preparation method step is:The base polyurethane prepolymer for use as of NCO end-group terminations is generated with polycarbonate polyol and di-isocyanate reaction;Being subsequently adding small molecule chain extender carries out chain extending reaction, and adding sulfonic acid type hydrophilic chain extender carries out sulfonating reaction, forms polyurethane from aggressiveness;Then add water dispersion at a high speed, and last vacuum distillation removes organic solvent, obtains finished product.Product of the invention have good thermal stability, it is safe and nontoxic, environment-friendly the characteristics of.

Description

A kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof
Technical field
The invention belongs to field of adhesive technology, and in particular to a kind of sulfonic acid type green environment protection adhesion agent and its preparation side Method.
Background technology
Polyurethane is that a class is synthesized by polycondensation by polyisocyanates (especially based on diisocyanate) and polyalcohol The general designation of resinae compound.Polyurethane is the block copolymer collectively constituted by soft and hard segments, generally, oligomer it is poly- Ester, PPG constitute soft section, and presentation is random to curl form;And polyisocyanates, small molecule chain extender, hydrophilic chain extension Agent etc. constitutes hard section, and its segment is all more stiff, and rod phase morphology is presented under normal temperature.The presence of soft or hard mutually embedding segment so that poly- ammonia Ester has superior filming performance, unique adhesive property and excellent pliability.Thus it is widely used in coating, gluing Agent, textile auxiliary and medicine and other fields.
In recent years, as " environment-friendly and green " is rooted in the hearts of the people, various countries put into effect every provisions of laws and regulations chemical products in succession Must develop towards nontoxic, innoxious, environment-friendly direction.Traditional organic solvent type polyurethane adhesive contains organic molten Agent and other poisonous auxiliary agents, due to its pollution and toxicity, are increasingly subject to limitation in use.And water-base polyurethane material due to Organic solvent is instead of using water, the characteristics of with safe and nontoxic, pollution-free, environmental protection, the poly- ammonia of organic solvent type is overcome The defect of ester.At present, the research of aqueous polyurethane is very more, and majority is, by self-emulsification, to be synthesized using dihydromethyl propionic acid Carboxylic acid type aqueous polyurethane.But carboxylic acid type hydrophilic chain extender generally forms weak acid and mild base salt, emulsion is uneven, and nertralizer is also easy Volatilization, limits its application in field of food;Water resistance, resistance to acids and bases, high and low temperature resistance all have with solvent-borne type after film forming A certain distance so that it is interrupted in the application of the aspects such as coating, adhesive.
At present, synthesis sulfonic acid type water-based polyurethane method the most practical is in chain extension process, to be introduced directly into small molecule Sulfonic acid type hydrophilic chain extender.Common this kind of chain extender has:1,4- butanediol -2- sodium sulfonates, 1,2- dihydroxy -3-N-morpholinopropanesulfonic acid Sodium, 2,4- diamino benzene sulfonic acids sodium, ethylenediamine base ethyl sulfonic acid sodium etc..Sulfonic acid type water-based polyurethane have well bond, it is water-fast, Heat resistance.Therefore, the research of sulfonic acid type water-based polyurethane is determined to win, and it is at aspects such as coating, adhesive, personal nursings Increasingly it is widely applied.This patent is using sulfonic acid type small molecule as hydrophilic chain extender, and the sulfonic acid type of preparation is aqueous poly- Urethane adhesive good thermal stability, it is environmentally friendly.
The content of the invention
The present invention is modified by sulfonic acid type hydrophilic chain extender to polyurethane adhesive, it is therefore an objective to provide a kind of sulfonic acid type Green environment protection adhesion agent and preparation method thereof, the sulfonic acid type green environment protection adhesion agent is prepared by each component of following weight portion:
100 parts of polycarbonate polyol
50 ~ 70 parts of diisocyanate
0.5 ~ 1.5 part of small molecule chain extender
0.02 ~ 0.1 part of dibutyl tin laurate
10 ~ 25 parts of organic solvent
1 ~ 10 part of sulfonic acid type hydrophilic chain extender
150 ~ 250 parts of deionized water;
Specifically preparation method step is:Equipped with N2Four mouthfuls of protection device, reflux condensate device, thermometer and mechanical agitator A certain amount of polycarbonate polyol is added in flask, 1 ~ 2 h is dehydrated under conditions of 120 DEG C and -0.01 MPa;Dehydration After be cooled to 60 ~ 80 DEG C, to the diisocyanate being slowly added into polycarbonate polyol, the h of insulation reaction 1 ~ 4, Obtain the performed polymer of polycarbonate polyol and diisocyanate;By polycarbonate polyol and the performed polymer liter of diisocyanate Temperature is subsequently adding small molecule chain extender and dibutyl tin laurate reacts 2 ~ 5 h to 80 ~ 100 DEG C;It is rapidly cooled to 10 ~ 25 DEG C, organic solvent diluting is added, adding sulfonic acid type hydrophilic chain extender carries out chain extending reaction 25 min, Zhi Houjia Enter deionized water, the min of dispersion and emulsion 30, last vacuum distillation is sloughed organic solvent, obtains sulfonic acid type green environment protection adhesion agent.
Heretofore described polycarbonate polyol is makrolon -1,4- butanediols, makrolon ethylene glycol, poly- carbon One or more arbitrary proportion mixture in acid esters diglycol, makrolon -1,6-HD.
Heretofore described diisocyanate is toluene di-isocyanate(TDI), 1,4- tetramethylene diisocyanates, 1,6- In hexamethylene diisocyanate, isoflurane chalcone diisocyanate, XDI, Methylcyclohexyl diisocyanate One or more arbitrary proportion mixture.
Heretofore described small molecule chain extender be ethylenediamine, 1,3- propane diamine, 1,4- butanediamine, 1,5- pentanediamines, One or more in 1,6- hexamethylene diamines, ethylene glycol, 1,6-HD, 1,4- butanediols, diglycol, neopentyl glycol Arbitrary proportion mixture.
Heretofore described organic solvent is 1-METHYLPYRROLIDONE, ethyl acetate, acetone, butanone, tetrahydrofuran, 1, One or more arbitrary proportion mixture in 4- dioxane.
Heretofore described sulfonic acid type hydrophilic chain extender be ethylenediamine base ethyl sulfonic acid sodium, 1,4- butanediol -2- sodium sulfonates, One or more arbitrary proportion mixture in 1,2- dihydroxy -3-N-morpholinopropanesulfonic acid sodium, 2,4- diamino benzene sulfonic acid sodium.
Beneficial effects of the present invention:A kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof, the sulfonic acid type of finished product is green Color environment-friendly adhesive is free of organic solvent, the characteristics of with safe and nontoxic, pollution-free, environmental protection, overcomes organic solvent type The defect of polyurethane, and the uniform good thermal stability of the penetrating odor without amine, emulsion;Using sulfonic acid type small molecule conduct Hydrophilic chain extender, the sulfonic acid type green environment protection adhesion agent good thermal stability of preparation is environmentally friendly.
Brief description of the drawings
Fig. 1 is modified sulfonic acid type green environment protection adhesion agent(Embodiment 3)With the thermal weight loss point of unmodified polyurethane Analysis spectrogram.
Specific embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention Rather than limitation the scope of the present invention.In addition, it is to be understood that after the content for having read instruction of the present invention, people in the art Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited Scope.
Embodiment 1
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters-BDO, at 120 DEG C, is dehydrated 1 h under conditions of -0.01 MPa;60 DEG C are cooled to, are lentamente added thereto Enter 32 g toluene di-isocyanate(TDI)s, the h of insulation reaction 4 obtains the performed polymer of low-molecular-weight;Performed polymer is warming up to 80 DEG C, so After add 0.6 g ethylenediamines small molecule chain extender and 0.01 g dibutyl tin laurates to react 2 h;10 DEG C are rapidly cooled to, 10 mL 1-METHYLPYRROLIDONEs are added to dilute, adding 2 g ethylenediamine base ethyl sulfonic acid sodium hydrophilic chain extenders carries out chain extending reaction 25 min;100 g deionized waters are added, the min of dispersion and emulsion 30, last vacuum distillation is sloughed 1-METHYLPYRROLIDONE, obtains sulphur Acid type green environment protection adhesion agent.
Embodiment 2
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters ethylene glycol, at 120 DEG C, is dehydrated 1 h under conditions of -0.01 MPa;70 DEG C are cooled to, 32 g are slowly added into thereto Isosorbide-5-Nitrae-tetramethylene diisocyanate, the h of insulation reaction 2, obtains the performed polymer of low-molecular-weight;Performed polymer is warming up to 90 DEG C, It is subsequently adding 0.6 g 1,6-HDs small molecule chain extender and 0.01 g dibutyl tin laurates reacts 2 h;Rapid cooling To 15 DEG C, the dilution of 10 mL ethyl acetate is added, adding 2 g BDO -2- sodium sulfonates hydrophilic chain extenders carries out chain extension React 25 min;100 g deionized waters are added, the min of dispersion and emulsion 30, last vacuum distillation is sloughed ethyl acetate, obtains sulphur Acid type green environment protection adhesion agent.
Embodiment 3
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters diglycol, at 120 DEG C, is dehydrated 2 h under conditions of -0.01 MPa;80 DEG C are cooled to, are lentamente added thereto Enter 32 g isoflurane chalcone diisocyanates, the h of insulation reaction 3 obtains the performed polymer of low-molecular-weight;Performed polymer is warming up to 100 DEG C, it is subsequently adding 0.6 g diglycols small molecule chain extender and 0.01 g dibutyl tin laurates reacts 2 h;Rapidly 15 DEG C are cooled to, the dilution of 10 mL acetone is added, 2 g 1 are added, 2- dihydroxy -3-N-morpholinopropanesulfonic acid sodium hydrophilic chain extender is expanded The min of chain reaction 25;100 g deionized waters are added, the min of dispersion and emulsion 30, last vacuum distillation is sloughed acetone, obtains sulfonic acid Type green environment protection adhesion agent.
Embodiment 4
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters -1,6- hexylene glycols, at 120 DEG C, are dehydrated 1.5 h under conditions of -0.01 MPa;65 DEG C are cooled to, thereto lentamente 32 g 1, hexamethylene-diisocyanate, the h of insulation reaction 3 are added to obtain the performed polymer of low-molecular-weight;Performed polymer is warming up to 88 DEG C, it is subsequently adding 0.6 g Putriscines small molecule chain extender and 0.01 g dibutyl tin laurates reacts 3.5 h;Rapidly 20 DEG C are cooled to, the dilution of 10 mL butanone is added, 2 g 2 are added, 4- diamino benzene sulfonic acid sodium hydrophilic chain extenders carry out chain extension React 25 min;100 g deionized waters are added, the min of dispersion and emulsion 30, last vacuum distillation is sloughed butanone, obtains sulfonic acid type Green environment protection adhesion agent.
Embodiment 5
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters-BDO, at 120 DEG C, is dehydrated 1 h under conditions of -0.01 MPa;72 DEG C are cooled to, are lentamente added thereto Enter 32 g isoflurane chalcone diisocyanates, the h of insulation reaction 2 obtains the performed polymer of low-molecular-weight;Performed polymer is warming up to 90 DEG C, 0.6 g 1 is subsequently adding, 6- hexamethylene diamines small molecule chain extender and 0.01 g dibutyl tin laurates react 5 h;It is rapid cold But to 10 DEG C, the dilution of 10 mL tetrahydrofurans is added, adds 2 g BDO -2- sodium sulfonate hydrophilic chain extenders and expanded The min of chain reaction 25;100 g deionized waters are added, the min of dispersion and emulsion 30, last vacuum distillation is sloughed tetrahydrofuran, obtained Sulfonic acid type green environment protection adhesion agent.
Embodiment 6
Equipped with N2The poly- carbon of 50 g is added in the four-hole boiling flask of protection device, reflux condensate device, thermometer and mechanical agitator Acid esters -1,6- hexylene glycols, at 120 DEG C, are dehydrated 1 h under conditions of -0.01 MPa;60 DEG C are cooled to, are lentamente added thereto Enter 32 g XDIs, the h of insulation reaction 4 obtains the performed polymer of low-molecular-weight;Performed polymer is warming up to 85 DEG C, it is subsequently adding 0.6 g BDOs small molecule chain extender and 0.01 g dibutyl tin laurates reacts 4.5 h;Rapidly 15 DEG C are cooled to, 10 mL1 are added, the dilution of 4- dioxane adds 2 g 1, the 2- dihydroxy-hydrophilic chain extension of 3-N-morpholinopropanesulfonic acid sodium Agent carries out the min of chain extending reaction 25;100 g deionized waters are added, Isosorbide-5-Nitrae-two is sloughed in the min of dispersion and emulsion 30, last vacuum distillation The ring of oxygen six, obtains sulfonic acid type green environment protection adhesion agent.
Embodiment 7
Gluing agent emulsion and standard aqueous polyurethane adhesive prepared by embodiment 3 take equivalent be poured on tetrafluoroethene plate into Film, places one week under the conditions of 25 DEG C, places into vacuum drying oven in being dried 2 days at 60 DEG C, obtains gathering for about 100 μm of thickness Urethane glue film.The heat resistance of glued membrane is weighed using thermogravimetric curve, Shimadzu TGA-50H thermogravimetric analyzers are used To test the thermogravimetric curve of glued membrane, the testing sample for weighing 6 ~ 10 mg is put into crucible, under nitrogen atmosphere heat flow rate It is 10 DEG C/min, 50 DEG C ~ 800 DEG C of Range of measuring temp.Two kinds of polyurethane materials as can be seen from Figure 1, the first stage is , from 50 DEG C ~ 280 DEG C, less, residual mass is essentially identical for the degraded difference of material, but works as the degradation temperature of hard section ammonia ester bond When temperature is increased to after 400 DEG C, comparative sample sustaining degradation, unmodified polyurethane samples residual mass is less than 10%, but Modified polyurethane samples residual mass is more than 60%;Illustrate gluing using sulfonic acid type environmental protection obtained in the inventive method The heat resistance of agent is greatly improved.It should be understood that embodiment 3 only illustrates modified sulfonic acid type water-based polyurethane as an example The heat endurance of adhesive is better than unmodified polyurethane.

Claims (6)

1. a kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof, it is characterised in that the sulfonic acid type environmental protection is gluing Agent is prepared by each component of following weight portion:
100 parts of polycarbonate polyol
50 ~ 70 parts of diisocyanate
0.5 ~ 1.5 part of small molecule chain extender
0.02 ~ 0.1 part of dibutyl tin laurate
10 ~ 25 parts of organic solvent
1 ~ 10 part of sulfonic acid type hydrophilic chain extender
150 ~ 250 parts of deionized water;
Specifically preparation method step is:Equipped with N2Four mouthfuls of protection device, reflux condensate device, thermometer and mechanical agitator A certain amount of polycarbonate polyol is added in flask, 1 ~ 2 h is dehydrated under conditions of 120 DEG C and -0.01 MPa;Dehydration After be cooled to 60 ~ 80 DEG C, to the diisocyanate being slowly added into polycarbonate polyol, the h of insulation reaction 1 ~ 4, Obtain the performed polymer of polycarbonate polyol and diisocyanate;By polycarbonate polyol and the performed polymer liter of diisocyanate Temperature is subsequently adding small molecule chain extender and dibutyl tin laurate reacts 2 ~ 5 h to 80 ~ 100 DEG C;It is rapidly cooled to 10 ~ 25 DEG C, organic solvent diluting is added, adding sulfonic acid type hydrophilic chain extender carries out chain extending reaction 25 min, Zhi Houjia Enter deionized water, the min of dispersion and emulsion 30, last vacuum distillation is sloughed organic solvent, obtains sulfonic acid type green environment protection adhesion agent.
2. a kind of sulfonic acid type green environment protection adhesion agent as claimed in claim 1 and preparation method thereof, it is characterised in that:Described Polycarbonate polyol is makrolon -1,4- butanediols, makrolon ethylene glycol, makrolon diglycol, poly- carbon One or more arbitrary proportion mixture in acid esters -1,6-HD.
3. a kind of sulfonic acid type green environment protection adhesion agent as claimed in claim 1 and preparation method thereof, it is characterised in that:Described Diisocyanate is toluene di-isocyanate(TDI), 1,4- tetramethylene diisocyanates, hexamethylene diisocyanate, isophorone two One or more arbitrary proportion in isocyanates, XDI, Methylcyclohexyl diisocyanate Mixture.
4. a kind of sulfonic acid type green environment protection adhesion agent as claimed in claim 1 and preparation method thereof, it is characterised in that:Described Small molecule chain extender is ethylenediamine, 1,3- propane diamine, 1,4- butanediamine, 1,5- pentanediamines, 1,6- hexamethylene diamines, ethylene glycol, 1,6- One or more arbitrary proportion mixture in hexylene glycol, 1,4- butanediols, diglycol, neopentyl glycol.
5. a kind of sulfonic acid type green environment protection adhesion agent as claimed in claim 1 and preparation method thereof, it is characterised in that:Described Organic solvent be one kind in 1-METHYLPYRROLIDONE, ethyl acetate, acetone, butanone, tetrahydrofuran, 1,4- dioxane or Various arbitrary proportion mixtures.
6. a kind of sulfonic acid type green environment protection adhesion agent as claimed in claim 1 and preparation method thereof, it is characterised in that:Described Sulfonic acid type hydrophilic chain extender be ethylenediamine base ethyl sulfonic acid sodium, 1,4- butanediol -2- sodium sulfonates, 1,2- dihydroxy -3-N-morpholinopropanesulfonic acid sodium, One or more arbitrary proportion mixture in 2,4- diamino benzene sulfonic acid sodium.
CN201611240127.6A 2016-12-29 2016-12-29 A kind of sulfonic acid type green environment protection adhesion agent and preparation method thereof Pending CN106753156A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101597369A (en) * 2008-06-06 2009-12-09 佛山市南海霸力化工制品有限公司 Contain high solid content polyurethane emulsion of alicyclic sulfonic acid type hydrophilic chain extending agent and preparation method thereof
CN102102005A (en) * 2010-12-13 2011-06-22 嘉兴禾欣化学工业有限公司 Preparation method of environmentally-friendly aqueous polyurethane adhesive
CN104530372A (en) * 2014-12-25 2015-04-22 张家港康得新光电材料有限公司 Water-based polyurethane and preparation method thereof, and composite film with water-based polyurethane
CN104910342A (en) * 2015-06-30 2015-09-16 东华大学 Preparation method of waterborne polyurethane
CN104031596B (en) * 2014-06-27 2016-01-13 重庆中科力泰高分子材料股份有限公司 A kind of low mold temperature water-based polyurethane adhesive and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101597369A (en) * 2008-06-06 2009-12-09 佛山市南海霸力化工制品有限公司 Contain high solid content polyurethane emulsion of alicyclic sulfonic acid type hydrophilic chain extending agent and preparation method thereof
CN102102005A (en) * 2010-12-13 2011-06-22 嘉兴禾欣化学工业有限公司 Preparation method of environmentally-friendly aqueous polyurethane adhesive
CN104031596B (en) * 2014-06-27 2016-01-13 重庆中科力泰高分子材料股份有限公司 A kind of low mold temperature water-based polyurethane adhesive and preparation method thereof
CN104530372A (en) * 2014-12-25 2015-04-22 张家港康得新光电材料有限公司 Water-based polyurethane and preparation method thereof, and composite film with water-based polyurethane
CN104910342A (en) * 2015-06-30 2015-09-16 东华大学 Preparation method of waterborne polyurethane

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
李和平: "《胶黏剂生产原理与技术》", 31 August 2009, 化学工业出版社 *
李广宇、李子东、宋颖韬、黄楚填: "《胶黏剂助剂》", 30 June 2009, 化学工业出版社 *
桑云森: "高固含量磺酸型水性聚氨酯胶黏剂的制备与表征", 《中国优秀硕士论文全文数据库 工程科技Ⅰ辑》 *

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Application publication date: 20170531